7-(4-amino-2-fluorophenoxy)-N,N',N'-trimethylthieno[3,2-b]pyridine-2-carbohydrazide → N1-(3-fluoro-4-(2-(1,2,2-trimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-methyl-N3-phenylmalonamide

Participants

Role	Name	HCID	Charge
Reactant	7-(4-amino-2-fluorophenoxy)-N,N',N'-trimethylthieno[3,2-b]pyridine-2-carbohydrazide	HCID 58790202	—
Reactant	N'-(4-(2-(2,2-Dimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-methoxyphenyl)malonamide	HCID 66649285	—
Product	N1-(3-fluoro-4-(2-(1,2,2-trimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-methyl-N3-phenylmalonamide	HCID 66649054	43%

Reaction Steps

Following the procedure described above for compound 236 (step 4, example 95, scheme 63) but replacing amine 239 with 7-(4-amino-2-fluorophenoxy)-N,N′,N′-trimethylthieno[3,2-b]pyridine-2-carbohydrazide (244), title compound 241 was obtained in 43% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.45 (s, 1H), 8.45 (d, J=5.4 Hz, 1H), 7.79 (d, J=13.3 Hz, 1H), 7.67 (s, 1H), 7.62-7.31 (m, 7H), 6.62 (d, J=5.4 Hz, 1H), 3.40 (s, 9H), 3.23 (s, 2H), 3.21 (s, 3H). MS (m/z): (M+1) 536.2 (100%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093264B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-6cf2ff1eadc345edb5c3a8c5742d4c5c
Source note	uspto-grants-2012_01